The first thing that I see investors get wrong all the time when evaluating equity crowdfunding investments is that they automatically assume that a fantastic company will make a great investment.

A great company and a great investment can be two completely different things.

As Warren Buffett wrote:

“Of course, a business with terrific economics can be a bad investment if it is bought at too high a price.” — 2016 shareholder letter

With that foundation in mind:

1. Start with valuation and investment terms. What price are you paying relative to the company’s progress, potential, and risks? What would the business need to achieve to deliver an attractive return from that starting valuation? Also understand what you’re buying: the security, ownership rights, and how future fundraising could dilute your stake. Those terms help determine how business success translates into investor returns. The SEC’s crowdfunding investor bulletin highlights valuation and differences in shareholder rights as important considerations. 

Remember that every great company can still be a bad investment opportunity if the valuation is too high.

Beyond that, the most useful data points depend on your objectives: financial returns, measurable impact, or some combination. I would focus on:

Evidence of traction appropriate to the stage. For an established business, examine revenue growth, customer retention, repeat purchases, and margins. For an earlier venture, look for product validation, paid pilots, technical milestones, or other evidence that reduces a specific risk. Distinguish demonstrated results from forecasts.

Market opportunity and competitive advantage. Look beyond a large headline market size. Who will actually buy, why will they choose this business, and what evidence supports its ability to reach those customers?

Cash runway and use of proceeds. How much cash is the business using, how long will the raise support operations, and what milestones should that funding achieve? Consider what happens if it raises only the minimum or growth takes longer than expected.

Measurable impact, if that is part of your goal. Look for defined outcomes, a baseline, and consistent reporting—for example, improvements in affordability or verified emissions reductions. Apply the same scrutiny to impact claims as to financial claims.

Underlying all of this is the team, especially before the business has established systems and processes. I’d look for relevant experience, complementary skills, commitment, and a compelling reason for tackling this particular problem. I’d also compare what they previously said they would accomplish with what they actually delivered. How candidly they discuss setbacks matters to me, as well as how they handle difficult investor questions in the Q&A, which can tell you a lot about a founder.

From a data-driven perspective, make sure the comparisons are meaningful: similar stages and business models, matching reporting periods, and consistent metric definitions. Revenue, bookings, and transaction volume measure different things. Check the dates and sources, and reconcile pitch-page claims with financial statements where possible.

Finally, consider how success could eventually return cash to investors. A growing business or a higher valuation on paper doesn’t, by itself, provide liquidity.

1. A list of 100 people's email addresses who have confirmed to you (the potential issuer) that they are as committed to the success of your venture as you are and can supply either time, talent or treasure to help you. 

2. Whatever financial review your raise requires from a CPA or similar financial firm.  The requirements change often. 

3. A report from a securities attorney on what is the most likely best issue you can make (equity, revenue share, convertible, SAFE, etc)

4. Due diligence answers.  Our questions are here: 

Traditionally, startup investing required dozens of hours of due diligence. Many investors are tempted to cut corners. Doing so risks building a poorly performing, low-impact portfolio.

Reg CF makes investing easier and faster inherently in two key ways. The portal is required to do some screening and background checks that angels had to do in the past. Furthermore, much greater required disclosures accelerate due diligence.

When investing for impact, I find most early-stage and small business issuers seeking impact don't have well-refined impact measurement in place. I look for impact that could be measured. 

For evaluating financial returns, I look for the ability to meet contractual expectations, as I focus on small business lending more often than equity investing, giving me an opportunity to earn money in the form of interest. When investing in equity, I look for the reasonable possibility of a tenfold return. 

Remember this axiom: if a deal is great in every way except valuation, it isn't a good deal. Valuation is essential!

To help with evaluating this, we have a free tool for members that guests can use for $12 per outing: https://SuperImpactScore.ai.

Bottom line: D&O for capital raises already exists. TigerMark is right-sized coverage at the right price for crowdfunding issuers.

Anytime a company raises outside capital and offers a security, the board or investors typically require D&O insurance. This isn't new. VC-backed, PE-backed, and institutionally funded companies have carried D&O coverage for decades. It's table stakes for professional capital formation.

The difference with crowdfunding is who you're raising from and how you're reaching them. Standard D&O policies were written for companies raising from accredited, institutional investors through private networks. Those policies often exclude claims arising from public offerings or general solicitation, which is exactly what Reg CF, Reg A+, and Reg D 506(c) involve.

That leaves crowdfunding issuers with two bad options: buy standard private company D&O that doesn't actually cover their real exposure, or overpay for full public company D&O designed for NASDAQ-listed companies.

That's why we built TigerMark. It's purpose-built for JOBS Act capital raises and covers what standard policies don't:

Claims from unaccredited investors in Reg CF and Reg A+ offerings
General solicitation exposure in Reg D 506(c) raises (where you're publicly advertising to accredited investors)
Specific compliance coverages for securities offerings not available elsewhere
Defense costs when an investor sues (securities litigation runs $250K-$500K+ before trial)
The ability to return investor principal if they allege wrongdoing
TigerMark also covers past or future Reg D 506(b) raises for traditional D&O risks, so your full capital-raising history is protected under one policy.

Beyond the coverage itself, TigerMark lets you showcase to your investors that your offering and company are safeguarded. You can display the TigerMark logo, share your policy summary, and demonstrate that you've taken the same governance steps that institutional-grade companies take.

Short answer: It's never too late, as long as no claim has already been filed.

D&O policies are claims-made, meaning they respond to claims made during the policy period regardless of when the underlying decision happened. TigerMark can backdate the retroactive date to match your offering date (your Form D, 1-A, or 1-C filing), so even if you bind coverage mid-raise or after closing, you're protected for decisions made since day one.

The only scenario that creates a true gap: waiting until after a claim is already filed or circumstances have been formally reported. At that point, that specific claim is uninsurable.

Best practice: Bind before or at launch. But if that window passed, bind now. The protection still applies retroactively to the start of your offering.

I wanted to make a productive investment.

There are 2 types of investing, speculative and productive. When I looked at my retirement account 10 years ago, it was largely index funds and ETFs full of very big corporations like Apple. I realized I wasn't funding Apple or any of the companies in the stock market because I was buying the shares from another investor, no value being created. 

I wanted to invest and fund the operations of businesses creating real value like a local community business or innovative clean tech. I wanted to make a productive investment.

Long story short, the only way the public can make a productive investment is through crowdfunding.

Great question. For me, the first ten years of RegCF were about proving the model works. And it does. Over $3.2 billion raised. More than 8,700 issuers. We built an entirely new asset class from scratch. That debate is over.

So where's the opportunity now? Three places.

First — secondary markets. We created millions of investors holding positions they can't sell. That's not a market, that's a waiting room. The moment we get credible secondary trading infrastructure, everything changes. You get price discovery. You get portfolio management. You get institutions actually paying attention. I've been pushing this at the SEC level because it's the single biggest unlock for this entire ecosystem.

Second — and this is where my research is headed — is what I call the Investomer Effect. We're finding that customers who invest in the companies they buy from behave completely differently. They spend more. They stick around longer. They recruit other customers. The next generation of winners won't be companies that stumble into this — they'll design for it. That's a massive opportunity in tooling, strategy, and frankly in how we think about what a "raise" even means.

Third — data. We now have ten years of public, structured data on early-stage capital formation and nobody is doing anything with it. We've been tracking every single RegCF offering since 2016. We can tell you survival rates, follow-on patterns, institutional crossover — 85% of these companies are still operating, by the way, not the 90% failure rate people assume. That dataset is the foundation for real analytics in private markets. Think of it as building the Bloomberg terminal for this space.

The bottom line? The first decade proved everyday people could invest in startups. The next decade is about proving those investments build wealth — through liquidity, better data, and companies that treat their investors like the customers they already are.

It’s a fair question - and one that nearly every founder, issuer, and portal marketer has asked at some point. The truth is, the rules aren’t stupid so much as stuck in another era. They were written before social media, analytics dashboards, or API-based ad targeting even existed, and they’ve never caught up with the way modern marketing actually works.

Under Regulation Crowdfunding (Reg CF), almost any public communication that even hints at a live investment opportunity is treated as solicitation. The SEC’s framework requires that offering-related messaging be limited to “tombstone-style” notices - factual, stripped of persuasion, and always directing readers back to the funding portal where the full disclosures live.

Why? Because the system is designed to prevent selective solicitation - the idea that someone could cherry-pick who sees an offering, giving certain investors an informational advantage. Regulators want everyone to have the same disclosures, at the same time, in the same place. On paper, that protects fairness and transparency. In practice, it makes every modern marketer feel like they’re working under rules written for the fax-machine era.

The irony is that today’s digital tools could make crowdfunding more transparent, measurable, and accountable - if only the rules allowed sensible use of them. Instead, compliance officers and ad managers spend their lives parsing whether a headline, emoji, or URL parameter “conditions the market.” It’s exhausting, expensive, and, yes, it feels damn stupid.

The hopeful news: the Crowdfunding Professional Association (CfPA) and other policy advocates are pressing the SEC to modernize these rules - to recognize that responsible data-driven marketing can coexist with investor protection. Until that happens, issuers and portals are left threading every campaign through a regulatory needle that was forged in the 1930s and polished once more in 2015. 

The key lesson I've learned over the past decade in the industry is that your campaign needs a marketing budget. I believe that with rare exceptions, a successful campaign needs a marketing budget equivalent to at least 10% of the total raise. One-third to half of that will need to be spent relatively early in the campaign.

Given this requirement, it is important to price your offering in such a way that you factor this in upfront.